3,4-Dimethylphenylboronic acid Chemical Properties

Melting point:

220°C

Boiling point:

304.9±52.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Powder

pka

8.89±0.10(Predicted)

color 

White to slightly beige

BRN 

2963858

CAS DataBase Reference

55499-43-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22-41-37/38

Safety Statements 

37/39-26-36/37-39

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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3,4-Dimethylphenylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 3,4-dimethylphenylboronic acid from trifluoromethanesulfonic acid-3,4-dimethylphenyl ester is as follows: in a 50 mL round-bottomed flask (equipped with a side arm, condenser, and stirring bar) triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), p-iodoiodobenzene (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol). The system was degassed by alternating vacuum and argon filling three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon atmosphere. After stirring at room temperature for 15 minutes, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and again degassed by alternating vacuum and argon filling three times. The reaction mixture was heated to reflux and maintained at reflux for 12 hours. Upon completion of the reaction, it was cooled to 0 °C and methanol (6 mL, note: exothermic reaction accompanied by hydrogen release) was slowly added. Stirring was continued for 15 minutes, followed by concentration under reduced pressure to remove all solvent to give a black solid. The solid was dissolved in 3M sodium hydroxide solution (8 mL) and washed with hexane (3 x 10 mL). The aqueous phase was cooled to 0 °C (ice bath) and acidified with concentrated hydrochloric acid to pH ≤ 1, at which point 3,4-dimethylphenylboronic acid precipitated as a white solid. The aqueous phase was extracted with ether (3 x 10 mL), the organic phases were combined, dried with magnesium sulfate and filtered. Finally, the solvent was removed by concentration under reduced pressure to give the white solid product 3,4-dimethylphenylboronic acid.

References

[1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583

3,4-Dimethylphenylboronic acid(55499-43-9)Related Product Information

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